Nickel-Catalyzed Enantioselective Reductive Conjugate Arylation and Heteroarylation via an Elementary Mechanism of 1,4-Addition

Luoqiang Zhang; Mengxin Zhao; Maoping Pu; Zhaoming Ma; Jingsong Zhou; Caiyou Chen; Yun Dong Wu; Yonggui Robin Chi; Jianrong Steve Zhou

doi:10.1021/jacs.2c05678

Nickel-Catalyzed Enantioselective Reductive Conjugate Arylation and Heteroarylation via an Elementary Mechanism of 1,4-Addition

Luoqiang Zhang, Mengxin Zhao, Maoping Pu, Zhaoming Ma, Jingsong Zhou, Caiyou Chen, Yun Dong Wu, Yonggui Robin Chi, Jianrong Steve Zhou^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically, experiments and calculations supported that an arylnickel(I) complex inserted to enones via an elementary 1,4-addition.

Original language	English
Pages (from-to)	20249-20257
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	144
Issue number	44
DOIs	https://doi.org/10.1021/jacs.2c05678
Publication status	Published - Nov 9 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/jacs.2c05678

Cite this

@article{feac79968883486c9a91bcbcd2536060,

title = "Nickel-Catalyzed Enantioselective Reductive Conjugate Arylation and Heteroarylation via an Elementary Mechanism of 1,4-Addition",

abstract = "A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically, experiments and calculations supported that an arylnickel(I) complex inserted to enones via an elementary 1,4-addition.",

author = "Luoqiang Zhang and Mengxin Zhao and Maoping Pu and Zhaoming Ma and Jingsong Zhou and Caiyou Chen and Wu, {Yun Dong} and Chi, {Yonggui Robin} and Zhou, {Jianrong Steve}",

year = "2022",

month = nov,

day = "9",

doi = "10.1021/jacs.2c05678",

language = "English",

volume = "144",

pages = "20249--20257",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "44",

}

TY - JOUR

T1 - Nickel-Catalyzed Enantioselective Reductive Conjugate Arylation and Heteroarylation via an Elementary Mechanism of 1,4-Addition

AU - Zhang, Luoqiang

AU - Zhao, Mengxin

AU - Pu, Maoping

AU - Ma, Zhaoming

AU - Zhou, Jingsong

AU - Chen, Caiyou

AU - Wu, Yun Dong

AU - Chi, Yonggui Robin

AU - Zhou, Jianrong Steve

PY - 2022/11/9

Y1 - 2022/11/9

N2 - A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically, experiments and calculations supported that an arylnickel(I) complex inserted to enones via an elementary 1,4-addition.

AB - A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically, experiments and calculations supported that an arylnickel(I) complex inserted to enones via an elementary 1,4-addition.

UR - http://www.scopus.com/inward/record.url?scp=85141493819&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85141493819&partnerID=8YFLogxK

U2 - 10.1021/jacs.2c05678

DO - 10.1021/jacs.2c05678

M3 - Article

C2 - 36315074

AN - SCOPUS:85141493819

SN - 0002-7863

VL - 144

SP - 20249

EP - 20257

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 44

ER -

Nickel-Catalyzed Enantioselective Reductive Conjugate Arylation and Heteroarylation via an Elementary Mechanism of 1,4-Addition

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this